Heterocyclic compound and organic electroluminescence device including the same

ABSTRACT

A heterocyclic compound and an organic electroluminescence device including the same, the heterocyclic compound being represented by Formula 1 below:

CROSS-REFERENCE TO RELATED APPLICATIONS

Korean Patent Application No. 10-2016-0148376, filed on Nov. 8, 2016, inthe Korean Intellectual Property Office, and entitled: “HeterocyclicCompound And Organic Electroluminescence Device Including The Same,” isincorporated by reference herein in its entirety.

BACKGROUND 1. Field

Embodiments relate to a heterocyclic compound and an organicelectroluminescence device including the same.

2. Description of the Related Art

The development of an organic electroluminescence display as an imagedisplay is being actively conducted. The organic electroluminescencedisplay is different from a liquid crystal display and is aself-luminescent display accomplishing displays via the recombination ofholes and electrons injected from a first electrode and a secondelectrode in an emission layer and via light emission from a luminescentmaterial including an organic compound in the emission layer.

As an organic electroluminescence device, an organic device including,for example, a first electrode, a hole transport layer disposed on thefirst electrode, an emission layer disposed on the hole transport layer,an electron transport layer disposed on the emission layer, and a secondelectrode disposed on the electron transport layer is well known. Holesare injected from the first electrode, and the injected holes move viathe hole transport layer and are injected into the emission layer.Meanwhile, electrons are injected from the second electrode, and theinjected electrons move via the electron transport layer and areinjected into the emission layer. The holes and electrons injected intothe emission layer recombine to produce excitons in the emission layer.The organic electroluminescence device emits light using light generatedby the transition of the excitons to a ground state. In addition, anembodiment of the configuration of the organic electroluminescencedevice is not limited thereto, but various modifications may bepossible.

SUMMARY

Embodiments are directed to a heterocyclic compound and an organicelectroluminescence device including the same.

The embodiments may be realized by providing a heterocyclic compoundrepresented by the following Formula 1:

wherein in Formula 1, X is NR₅, O, or S, R₁ to R₄ are each independentlya hydrogen atom, a substituted or unsubstituted amino group, asubstituted or unsubstituted silyl group, a substituted or unsubstitutedalkoxy group, a substituted or unsubstituted aryloxy group, asubstituted or unsubstituted alkythio group, a substituted orunsubstituted arylthio group, a substituted or unsubstituted borylgroup, a substituted or unsubstituted sulfoxy group, a substituted orunsubstituted phosphine oxide group, a substituted or unsubstitutedcarbonyl group, a substituted or unsubstituted alkyl group having 1 to10 carbon atoms, a substituted or unsubstituted aralkyl group, asubstituted or unsubstituted aryl group having 6 to 30 ring carbonatoms, or a substituted or unsubstituted heteroaryl group having 2 to 30ring carbon atoms, R₁ to R₄ being separate or forming a ring viacombination of adjacent groups with each other, R₅ is a hydrogen atom, adeuterium atom, a substituted or unsubstituted silyl group, asubstituted or unsubstituted boryl group, a substituted or unsubstitutedsulfoxy group, a substituted or unsubstituted phosphine oxide group, asubstituted or unsubstituted carbonyl group, a substituted orunsubstituted alkyl group having 1 to 10 carbon atoms, a substituted orunsubstituted aralkyl group, a substituted or unsubstituted aryl grouphaving 6 to 30 ring carbon atoms, or a substituted or unsubstitutedheteroaryl group having 2 to 30 ring carbon atoms, at least one of R₁ toR₄ is a substituted or unsubstituted silyl group, a substituted orunsubstituted alkoxy group, a substituted or unsubstituted aryloxygroup, a substituted or unsubstituted alkythio group, a substituted orunsubstituted arylthio group, a substituted or unsubstituted borylgroup, a substituted or unsubstituted aralkyl group, a substituted orunsubstituted sulfoxy group, or a substituted or unsubstituted phosphineoxide group, and at least two of R₁ to R₄ are not an aryl group or aheteroaryl group.

Two of R₁ to R₄ may each independently be an aryl group or a heteroarylgroup, and at least one of the remaining ones of R₁ to R₄ may be asubstituted or unsubstituted silyl group, a substituted or unsubstitutedalkoxy group, a substituted or unsubstituted aryloxy group, asubstituted or unsubstituted alkythio group, a substituted orunsubstituted arylthio group, a substituted or unsubstituted borylgroup, a substituted or unsubstituted aralkyl group, a substituted orunsubstituted sulfoxy group, or a substituted or unsubstituted phosphineoxide group.

Two of R₁ to R₄ may each independently be a substituted or unsubstitutedaryl group having 6 to 15 ring carbon atoms or a substituted orunsubstituted heteroaryl group having 2 to 15 ring carbon atoms, and atleast one of the remaining ones of R₁ to R₄ may be a substituted orunsubstituted silyl group.

Two of R₁ to R₄ may each independently be a substituted or unsubstitutedphenyl group, and at least one of the remaining ones of R₁ to R₄ may bea triphenylsilyl group.

X may be NR₅.

R₅ may be a substituted or unsubstituted aryl group having 6 to 15 ringcarbon atoms.

R₅ may be a substituted or unsubstituted phenyl group.

X may be NR₅, at least one of R₁ to R₅ may be a group represented by-L₁-Y₁, L₁ may be a substituted or unsubstituted arylene group having 6to 30 ring carbon atoms, and Y₁ may be a substituted or unsubstitutedsilyl group, a substituted or unsubstituted pyrrolyl group, asubstituted or unsubstituted thienyl group, or a substituted orunsubstituted furanyl group.

The compound represented by Formula 1 may be represented by thefollowing Formula 2:

wherein in Formula 2, n may be an integer of 1 to 3, when n is 2 or 3, aplurality of R₁ to R₄ may be the same or different from each other, L₃may be a direct linkage or a substituted or unsubstituted aryl grouphaving 6 to 30 ring carbon atoms, and R₁ to R₄ may be defined the sameas those of Formula 1.

The compound represented by Formula 1 may be represented by thefollowing Formula 3:

wherein in Formula 3, m may be an integer of 1 to 3, when m is 2 or 3, aplurality of R₁, R₂, and R₄ may be the same or different from eachother, L₄ may be a direct linkage or a substituted or unsubstituted arylgroup having 6 to 30 ring carbon atoms, and X, R₁, R₂, and R₄ may bedefined the same as those of Formula 1.

The compound represented by Formula 1 may be represented by thefollowing Formula 4:

wherein in Formula 4, q may be an integer of 1 to 3, when q is 2 or 3, aplurality of R₁ to R₃ may be the same or different from each other, L₅may be a direct linkage or a substituted or unsubstituted aryl grouphaving 6 to 30 ring carbon atoms, and X, and R₁ to R₃ may be defined thesame as those of Formula 1.

The compound represented by Formula 1 may be represented by thefollowing Formula 5:

wherein Formula 5, W may be O, S, PR₈, S═O, SO₂, P═OR₉, CR₁₀R₁₁, orSiR₁₂R₁₃, R₆ to R₁₃ may each independently be a hydrogen atom, adeuterium atom, a substituted or unsubstituted alkyl group having 1 to10 carbon atoms, a substituted or unsubstituted aryl group having 6 to30 ring carbon atoms, or a substituted or unsubstituted heteroaryl grouphaving 2 to 30 ring carbon atoms, a and b may each independently be aninteger of 0 to 4, and X, R₁ and R₄ may be defined the same as those ofFormula 1.

The heterocyclic compound represented by Formula 1 may be a compound ofthe following Compound Group 1:

The embodiments may be realized by providing an organicelectroluminescence device including a first electrode; a hole transportregion on the first electrode; an emission layer on the hole transportregion; an electron transport region on the emission layer; and a secondelectrode on the electron transport region, wherein the hole transportregion includes a heterocyclic compound represented by the followingFormula 1:

wherein in Formula 1. X is NR₅, O or S, R₁ to R₄ are each independentlya hydrogen atom, a substituted or unsubstituted amino group, asubstituted or unsubstituted silyl group, a substituted or unsubstitutedalkoxy group, a substituted or unsubstituted aryloxy group, asubstituted or unsubstituted alkythio group, a substituted orunsubstituted arylthio group, a substituted or unsubstituted borylgroup, a substituted or unsubstituted sulfoxy group, a substituted orunsubstituted phosphine oxide group, a substituted or unsubstitutedcarbonyl group, a substituted or unsubstituted alkyl group having 1 to10 carbon atoms, a substituted or unsubstituted aralkyl group, asubstituted or unsubstituted aryl group having 6 to 30 ring carbonatoms, or a substituted or unsubstituted heteroaryl group having 2 to 30ring carbon atoms, R₁ to R₄ being separate or forming a ring viacombination of adjacent groups with each other, R₅ is a hydrogen atom, adeuterium atom, a substituted or unsubstituted silyl group, asubstituted or unsubstituted boryl group, a substituted or unsubstitutedsulfoxy group, a substituted or unsubstituted phosphine oxide group, asubstituted or unsubstituted carbonyl group, a substituted orunsubstituted alkyl group having 1 to 10 carbon atoms, a substituted orunsubstituted aralkyl group, a substituted or unsubstituted aryl grouphaving 6 to 30 ring carbon atoms, or a substituted or unsubstitutedheteroaryl group having 2 to 30 ring carbon atoms, at least one of R₁ toR₄ is a substituted or unsubstituted silyl group, a substituted orunsubstituted alkoxy group, a substituted or unsubstituted aryloxygroup, a substituted or unsubstituted alkythio group, a substituted orunsubstituted arylthio group, a substituted or unsubstituted borylgroup, a substituted or unsubstituted aralkyl group, a substituted orunsubstituted sulfoxy group, or a substituted or unsubstituted phosphineoxide group, and at least two of R₁ to R₄ are not an aryl group or aheteroaryl group.

Two of R₁ to R₄ may each independently be an aryl group or a heteroarylgroup, and at least one of the remaining ones of R₁ to R₄ may be asubstituted or unsubstituted silyl group, a substituted or unsubstitutedalkoxy group, a substituted or unsubstituted aryloxy group, asubstituted or unsubstituted alkythio group, a substituted orunsubstituted arylthio group, a substituted or unsubstituted borylgroup, a substituted or unsubstituted aralkyl group, a substituted orunsubstituted sulfoxy group, or a substituted or unsubstituted phosphineoxide group.

X may be NR₅, at least one of R₁ to R₅ may be a group represented by-L₁-Y₁, L₁ may be a substituted or unsubstituted arylene group having 6to 30 ring carbon atoms, and Y₁ may be a substituted or unsubstitutedsilyl group, a substituted or unsubstituted pyrrolyl group, asubstituted or unsubstituted thienyl group, or a substituted orunsubstituted furanyl group.

X may be NR₅, and R₅ may be the same as defined in claim 14.

The compound represented by Formula 1 may be represented by one of thefollowing Formulae 2 to 4:

wherein in Formulae 2 to 4, n, m, and p may each independently be aninteger of 1 to 3, when n is 2 or 3, a plurality of R₁ to R₄ may be thesame or different from each other, when m is 2 or 3, a plurality of R₁,R₂, and R₄ may be the same or different from each other, when q is 2 or3, a plurality of R₁ to R₃ may be the same or different from each other,L₃ to L₅ may each independently be a direct linkage or a substituted orunsubstituted aryl group having 6 to 30 ring carbon atoms, and X, and R₁to R₄ may be defined the same as those of Formula 1.

The compound represented by Formula 1 may be represented by thefollowing Formula 5:

wherein in Formula 5, W may be O, S, PR₈, S═O, SO₂, P═OR₉, CR₁₀R₁₁, orSiR₁₂R₁₃, R₆ to R₁₃ may each independently be a hydrogen atom, adeuterium atom, a substituted or unsubstituted alkyl group having 1 to10 carbon atoms, a substituted or unsubstituted aryl group having 6 to30 ring carbon atoms, or a substituted or unsubstituted heteroaryl grouphaving 2 to 30 ring carbon atoms, a and b may each independently be aninteger of 0 to 4, and X, R₁ and R₄ may be defined the same as those ofFormula 1.

The heterocyclic compound represented by Formula 1 may be a compound ofthe following Compound Group 1:

BRIEF DESCRIPTION OF THE DRAWINGS

Features will be apparent to those of skill in the art by describing indetail exemplary embodiments with reference to the attached drawings inwhich:

FIG. 1 illustrates a cross-sectional view of an organicelectroluminescence device according to an embodiment of the presentdisclosure; and

FIG. 2 illustrates a cross-sectional view of an organicelectroluminescence device according to an embodiment of the presentdisclosure.

DETAILED DESCRIPTION

Example embodiments will now be described more fully hereinafter withreference to the accompanying drawings; however, they may be embodied indifferent forms and should not be construed as limited to theembodiments set forth herein. Rather, these embodiments are provided sothat this disclosure will be thorough and complete, and will fullyconvey exemplary implementations to those skilled in the art.

Like reference numerals refer to like elements for explaining eachdrawing. In the drawings, the sizes of elements may be enlarged forclarity of the present disclosure. It will be understood that, althoughthe terms first, second, etc. may be used herein to describe variouselements, these elements should not be limited by these terms. Theseterms are only used to distinguish one element from another element. Forexample, a first element discussed below could be termed a secondelement, and similarly, a second element could be termed a firstelement. As used herein, the singular forms are intended to include theplural forms as well, unless the context clearly indicates otherwise.

It will be further understood that the terms “includes,” “including,”“comprises,” or “comprising,” when used in this specification, specifythe presence of stated features, numerals, steps, operations, elements,parts, or a combination thereof, but do not preclude the presence oraddition of one or more other features, numerals, steps, operations,elements, parts, or a combination thereof. It will also be understoodthat when a layer, a film, a region, a plate, etc. is referred to asbeing ‘on’ another part, it can be directly on the other part, orintervening layers may also be present. On the contrary, when a layer, afilm, a region, a plate, etc. is referred to as being ‘under’ anotherpart, it can be directly under the other part, or intervening layers mayalso be present. As used herein, the term “or” is not an exclusive term,e.g., A or B includes A, B, or A and B.

In the present disclosure,

* means a part to be connected, e.g., a bonding site.

In the present disclosure, “substituted or unsubstituted” may meansubstituted with deuterium, halogen, cyano, nitro, amino, silyl, boron,arylamine, phosphine oxide, phosphine sulfide, alkyl, alkenyl, aryl, andheteroaryl or unsubstituted. In addition, each of the substituentillustrated above may be substituted or unsubstituted. For example,biphenyl may be interpreted as aryl, or phenyl substituted with phenyl.

In the present disclosure, the description of forming a ring bycombining with an adjacent group may mean forming substituted orunsubstituted cyclic hydrocarbon, or substituted or unsubstitutedheterocycle by combining with an adjacent group. The cyclic hydrocarbonmay include aliphatic cyclic hydrocarbon and aromatic cyclichydrocarbon. The heterocycle may include aliphatic heterocycle andaromatic heterocycle. The cyclic hydrocarbon and heterocycle may be amonocycle or polycycle. In addition, the ring formed by combining withan adjacent group may be connected with another ring to form a spirostructure.

In the present disclosure, the term “adjacent groups” may mean asubstituent substituted with an atom directly connected with anotheratom substituted with a corresponding substituent, a differentsubstituent substituted with an atom substituted with a correspondingsubstituent, or a substituent disposed stereoscopically at the nearestposition to a corresponding substituent. For example, two methyl groupsin 1,2-dimethylbenzene may be interpreted as “adjacent groups”, and twoethyl groups in 1,1-diethylcyclopentene may be interpreted as “adjacentgroups”.

In the present disclosure, a halogen atom may include a fluorine atom, achlorine atom, a bromine atom, or an iodine atom.

In the present disclosure, the alkyl may have a linear or branched chainor a cycle shape. The carbon number of the alkyl may be 1 to 30, 1 to20, 1 to 10, or 1 to 6. Examples of the alkyl may include methyl, ethyl,n-propyl, isopropyl, n-butyl, s-butyl, t-butyl, i-butyl, 2-ethylbutyl,3,3-dimethylbutyl, n-pentyl, i-pentyl, neopentyl, t-pentyl, cyclopentyl,1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl,n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl,4-methylcyclohexyl, 4-t-butylcyclohexyl, n-heptyl, 1-methylheptyl,2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, t-octyl,2-ethyloctyl, 2-butyloctyl, 2-hexyloctyl, 3,7-dimethyloctyl, cyclooctyl,n-nonyl, n-decyl, adamantyl, 2-ethyldecyl, 2-butyldecyl, 2-hexyldecyl,2-octyldecyl, n-undecyl, n-dodecyl, 2-ethyldodecyl, 2-butyldodecyl,2-hexyldodecyl, 2-octyldodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl,n-hexadecyl, 2-ethylhexadecyl, 2-butylhexadecyl, 2-hexylhexadecyl,2-octylhexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, n-eicosyl,2-ethyl eicosyl, 2-butyl eicosyl, 2-hexyl eicosyl, 2-octyl eicosyl,n-henicosyl, n-docosyl, n-tricosyl, n-tetracosyl, n-pentacosyl,n-hexacosyl, n-heptacosyl, n-octacosyl, n-nonacosyl, n-triacontyl, etc.,without limitation.

In the present disclosure, the aryl means an optional functional groupor substituent derived from aromatic cyclic hydrocarbon. The aryl may bemonocyclic aryl or polycyclic aryl. The carbon number of the aryl forforming a ring may be 6 to 30, 6 to 20, or 6 to 15. Examples of the arylmay include phenyl, naphthyl, fluorenyl, anthracenyl, phenanthryl,biphenyl, terphenyl, quaterphenyl, quinqphenyl, sexiphenyl,triphenylene, pyrenyl, benzofluoranthenyl, chrysenyl, etc., withoutlimitation.

In the present disclosure, fluorenyl may be substituted, or twosubstituents may be combined with each other to form a spiro structure.

In the present disclosure, the explanation on the aryl may be applied tothe arylene, except for the case where the arylene is divalent.

In the present disclosure, the heteroaryl may be heteroaryl including atleast one of O, N, P Si, or S as a heteroatom. The carbon number of theheteroaryl for forming a ring may be 2 to 30, 2 to 20, or 2 to 15.Examples of the heteroaryl may include monocyclic heteroaryl orpolycyclic heteroaryl. The polycyclic heteroaryl may have a two ringstructure or a three ring structure. Examples of the heteroaryl mayinclude thienyl, furanyl, pyrrolyl, imidazole, thiazole, oxazole,oxadiazole, triazole, pyridyl, bipyridyl, pyrimidyl, triazine, triazole,acridyl, pyridazine, pyrazinyl, quinolinyl, quinazoline, quinoxalinyl,phenoxazyl, phthalazinyl, pyrido pyrimidinyl, pyrido pyrazinyl, pyrazinopyrazinyl, isoquinoline, indole, carbazole, N-arylcarbazole,N-heteroaryl carbazole, N-alkyl carbazole, benzoxazole, benzoimidazole,benzothiazole, benzocarbazole, benzothienyl dibenzothiophenyl,thienothienyl, benzofuranyl, phenanthroline, thiazolyl, isooxazolyl,oxadiazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl,dibenzosilole, dibenzofuranyl, etc., without limitation.

In the present disclosure, the silyl may include alkylsilyl andarylsilyl. Examples of the silyl may include trimethylsilyl,triethylsilyl, t-butyldimethylsilyl, vinyldimethylsilyl,propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, etc.,without limitation.

In the present disclosure, the boryl group (boron group) may includealkyl boron and aryl boron. Examples of the boron group may includetrimethylboron, triethylboron, t-butyldimethylboron, triphenylboron,diphenylboron, phenylboron, etc., without limitation.

In the present disclosure, the alkenyl may be linear or branched. Thecarbon number is not specifically limited, but may be 2 to 30, 2 to 20,or 2 to 10. Examples of the alkenyl may include vinyl, 1-butenyl,1-pentenyl, 1,3-butadienyl aryl, styrenyl, styrylvinyl, etc., withoutlimitation.

In the present disclosure, the carbon number of the amino group is notspecifically limited, but may be 1 to 30. The amino group may include analkyl amino group and aryl amino group. Examples of the amino group mayinclude methylamino, dimethylamino, phenylamino, diphenylamino,naphthylamino, 9-methyl-anthracenylamino, triphenylamino, etc., withoutlimitation.

In the present disclosure, the carbon number of carbonyl group is notspecifically limited, and may be 1 to 40, 1 to 30, or 1 to 20. Forexample, the carbonyl group may have the structures below, but anembodiment of the present disclosure is not limited thereto.

In the present disclosure, the sulfoxy group may include an alkylsulfoxy group and an aryl sulfoxy group.

In the present disclosure, the alkoxy group may have a linear chain, abranched chain, or a cyclic chain. The carbon number of the alkoxy groupis not specifically limited and may be, for example, 1 to 20, or 1 to10. Examples of the alkoxy group include methoxy, ethoxy, n-propoxy,isopropoxy, butoxy, pentyloxy, hexyloxy, octyloxy, nonyloxy, decyloxy,benzyloxy, or the like. However, an embodiment of the present disclosureis not limited thereto.

In the present disclosure, examples of an aryl group among aryloxy,arylthio, arylsulfoxy, aralkyl, arylamino, aryl sulfoxy, aryl boronyl,aryl silyl, and aryl phosphine, are the same as described above.

In the present disclosure, examples of an alkyl group among aralkyl,alkylthio, alkylsulfoxy, alkylaryl, alkylamino, alkyl boronyl, and alkylsilyl are the same as described above.

Hereinafter, the heterocyclic compound according to an embodiment of thepresent disclosure will be explained.

The heterocyclic compound according to an embodiment of the presentdisclosure may be represented by Formula 1 below.

In Formula 1, X may be, e.g., NR₅, O or S. R₁ to R₄, may eachindependently be or include, e.g., a hydrogen atom, a substituted orunsubstituted amino group, a substituted or unsubstituted silyl group, asubstituted or unsubstituted alkoxy group, a substituted orunsubstituted aryloxy group, a substituted or unsubstituted alkythiogroup, a substituted or unsubstituted arylthio group, a substituted orunsubstituted boryl group, a substituted or unsubstituted sulfoxy group,a substituted or unsubstituted phosphine oxide group, a substituted orunsubstituted carbonyl group, a substituted or unsubstituted alkyl grouphaving 1 to 10 carbon atoms, a substituted or unsubstituted aralkylgroup, a substituted or unsubstituted aryl group having 6 to 30 ringcarbon atoms, or a substituted or unsubstituted heteroaryl group having2 to 30 ring carbon atoms. In an implementation, R₁ to R₄, may beseparate or form a ring via the combination of adjacent groups from eachother. R₅ may be or may include, e.g., a hydrogen atom, a deuteriumatom, a substituted or unsubstituted silyl group, a substituted orunsubstituted boryl group, a substituted or unsubstituted sulfoxy group,a substituted or unsubstituted phosphine oxide group, a substituted orunsubstituted carbonyl group, a substituted or unsubstituted alkyl grouphaving 1 to 10 carbon atoms, a substituted or unsubstituted aralkylgroup, a substituted or unsubstituted aryl group having 6 to 30 ringcarbon atoms, or a substituted or unsubstituted heteroaryl group having2 to 30 ring carbon atoms.

In an implementation, in Formula 1, at least one of R₁ to R₄ may be ormay include, e.g., a substituted or unsubstituted silyl group, asubstituted or unsubstituted alkoxy group, a substituted orunsubstituted aryloxy group, a substituted or unsubstituted alkythiogroup, a substituted or unsubstituted arylthio group, a substituted orunsubstituted boryl group, a substituted or unsubstituted aralkyl group,a substituted or unsubstituted sulfoxy group, a substituted orunsubstituted phosphine oxide group.

In an implementation, in Formula 1, at least two of R₁ to R₄ may not bethe aryl group or the heteroaryl group. For example, a sum of a numberof aryl groups and heteroaryl groups among R₁ to R₄ may be 2 or less.Here, the aryl group means a substituted or unsubstituted aryl grouphaving 6 to 30 ring carbon atoms, and the heteroaryl group means asubstituted or unsubstituted heteroaryl group having 2 to 30 ring carbonatoms.

In an implementation, in Formula 1, the sum of the number of the arylgroup and the heteroaryl group among R₁ to R₄ may be, e.g., 2. In animplementation, in Formula 1, two of R₁ to R₄ may each independently bean aryl group or a heteroaryl group, and at least one of the remainingtwo thereof may be a substituted or unsubstituted silyl group, asubstituted or unsubstituted alkoxy group, a substituted orunsubstituted aryloxy group, a substituted or unsubstituted alkylthiogroup, a substituted or unsubstituted arylthio group, a substituted orunsubstituted boryl group, a substituted or unsubstituted aralkyl group,a substituted or unsubstituted sulfoxy group, or a substituted orunsubstituted phosphine oxide group. In an implementation, the carbonnumber of the aryl group forming a ring may be 6 to 15, and the carbonnumber of the heteroaryl group forming a ring may be 2 to 15.

In an implementation, in Formula 1, two of R₁ to R₄ may eachindependently be an aryl group or a heteroaryl group, and at least oneof the remaining two thereof may be a substituted or unsubstituted silylgroup. In an implementation, at least one of the remaining two may be anarylsilyl group, an implementation, at least one of the remaining twothereof may be a substituted or unsubstituted phenylsilyl group, asubstituted or unsubstituted diphenylsilyl group, or a substituted orunsubstituted triphenylsilyl group, an implementation, at least one ofthe remaining two thereof may be, e.g., a substituted or unsubstitutedtriphenylsilyl group.

In an implementation, in Formula 1, two of R₁ to R₄ may eachindependently be or include, e.g., a substituted or unsubstituted phenylgroup, and at least one of the remaining two thereof may be, e.g., atriphenylsilyl group. In an implementation, the compound represented byFormula 1 may be represented by one of the following Formulae 1-1 to1-4.

In Formulae 1-1 to 1-4, Ph may be, e.g., a substituted or unsubstitutedphenyl group, E₁ and E₂ may each independently be, e.g., a hydrogenatom, or a substituted or unsubstituted triphenylsilyl group, where atleast one of E₁ and E₂ is a substituted or unsubstituted triphenylsilylgroup. Ph may be a phenyl group unsubstituted or substituted with anarylsilyl group. Ph may be a phenyl group unsubstituted or substitutedwith a triphenylsilyl group.

In an implementation, in Formula 1, two of R₁ to R₄ may eachindependently be, e.g., an aryl group or a heteroaryl group. In animplementation, one may be a substituted or unsubstituted phenyl group,and the other one may be a substituted or unsubstituted monocyclicheteroaryl group. In an implementation, both two among R₁ to R₄ may besubstituted or unsubstituted aryl groups. In this case, two aryl groupsmay be the same or different. In an implementation, two among R₁ to R₄may both be substituted or unsubstituted heteroaryl groups, and twoheteroaryl groups may be the same or different.

In an implementation, in Formula 1, two of R₁ to R₄ may eachindependently be, e.g., an aryl group or a heteroaryl group, and atleast one of the remaining two thereof may be, e.g., a substituted orunsubstituted aralkyl group. For example, at least one of the remainingtwo thereof may be a triphenylalkyl group.

In an implementation, in Formula 1, X may be, e.g., NR₅. For example, inFormula 1, X may be NR₅ and R₅ may be a substituted or unsubstitutedaryl group having 6 to 15 ring carbon atoms. For example, R₅ may be asubstituted or unsubstituted phenyl group. In an implementation, thecompound represented by Formula 1 may be represented by Formula 1-5below. In an implementation, in Formula 1, X may be O or S.

In Formula 1-5, Ph may be, e.g., a substituted or unsubstituted phenylgroup, and R₁ to R₄ are the same as described above. Ph may be a phenylgroup unsubstituted or substituted with an arylsilyl group, e.g., aphenyl group unsubstituted or substituted with a triphenylsilyl group.

In an implementation, in Formula 1, X may be NR₅, and at least one of R₁to R₅ may be a group represented by -L₁-Y₁. L₁ may be or may include,e.g., a substituted or unsubstituted arylene group having 6 to 30 ringcarbon atoms. Y₁ may be or may include, e.g., a substituted orunsubstituted silyl group, a substituted or unsubstituted pyrrolylgroup, a substituted or unsubstituted thienyl group, or a substituted orunsubstituted furanyl group.

In an implementation, in Formula 1, X may be NR₅, and R₅ may berepresented by -L₁-Y₁. In an implementation, the compound represented byFormula 1 may be represented by, e.g., Formula 2 below.

In Formula 2, n may be, e.g., an integer of 1 to 3, L₃ may be, e.g., adirect linkage or a substituted or unsubstituted aryl group having 6 to30 ring carbon atoms, and R₁ to R₄ may be the same as described above.For example, X may be NR₅, and R₅ may be a group having a substitutionscheme or pattern such that the heterocyclic compound includes at leastone more pyrrolyl moiety (when n is 2 or 3).

In an implementation, the direct linage may include a single bond.

In an implementation, in Formula 2, in a case where n is 2 or more, aplurality of R₁ to R₄ may be the same or different. For example, inFormula 2, in a case where n is 2 or more, structures in parentheses maybe the same or different.

In an implementation, in Formula 2, in a case where n is 1, L₃ may be amonovalent group, in a case where n is 2, L₃ may be a divalent group,and in a case where n is 3, L₃ may be a trivalent group.

In an implementation, in Formula 2, n may be 2, and L₃ may be asubstituted or unsubstituted arylene group having 6 to 15 ring carbonatoms. In an implementation, in Formula 2, n may be 2, and L₃ may be asubstituted or unsubstituted monocyclic arylene group. In animplementation, in Formula 2, n may be 2, and L₃ may be a substituted orunsubstituted phenylene group, e.g., a p-phenylene group or anm-phenylene group.

In an implementation, in Formula 1, at least one of R₁ to R₄ may be agroup represented by -L₁-Y₁. In an implementation, in Formula 1, one ofR₁ to R₄ may be a group represented by -L₁-Y₁. In an implementation, thecompound represented by Formula 1 may be represented by, e.g., Formula 3below.

In Formula 3, m may be, e.g., an integer of 1 to 3, L₄ may be, e.g., adirect linkage or a substituted or unsubstituted aryl group having 6 to30 ring carbon atoms, and X. R₁, R₂, and R₄ may be the same as describedabove. For example, R₃ may be a group having a substitution scheme orpattern such that the heterocyclic compound includes at least one morepyrrolyl moiety (when m is 2 or 3).

In Formula 3, in a case where m is 2 or more, a plurality of R₁, R₂, andR₄ may be the same or different. For example, in Formula 3, in a casewhere m is 2 or more, structures in parentheses may be the same ordifferent.

In Formula 3, in a case where m is 1, L₄ may be a monovalent group, in acase where m is 2, L₄ may be a divalent group, and in a case where m is3, L₄ may be a trivalent group.

In an implementation, in Formula 3, m may be 2, and L₄ may be or mayinclude, e.g., a substituted or unsubstituted arylene group having 6 to15 ring carbon atoms. In an implementation, in Formula 3, m may be 2,and L₄ may be or may include, e.g., a substituted or unsubstitutedmonocyclic arylene group. In an implementation, in Formula 3, m may be2, and L₄ may be a substituted or unsubstituted phenylene group, e.g.,an m-phenylene group. Formula 3 corresponds to Formula 1 where R₃ is agroup represented by -L₁-Y₁.

In an implementation, in Formula 3, X may be, e.g., NR₅.

In an implementation, in Formula 3, at least one of R₁, R₂, and R₄ maybe, e.g., a substituted or unsubstituted silyl group. In animplementation, in Formula 3, at least two of R₁, R₂, and R₄ may not bean aryl group or a heteroaryl group.

In an implementation, the compound represented by Formula 1 may berepresented by, e.g., Formula 4 below.

In Formula 4, q may be, e.g., an integer of 1 to 3, L₅ may be or mayinclude, e.g., a direct linkage or a substituted or unsubstituted arylgroup having 6 to 30 ring carbon atoms, and X and R₁ to R₃ may be thesame as described above. For example, R₄ may be a group having asubstitution scheme or pattern such that the heterocyclic compoundincludes at least one more pyrrolyl moiety (when m is 2 or 3).

In Formula 4, in a case where q is 2 or more, a plurality of R₁ to R₃may be the same or different. For example, in Formula 4, in a case whereq is 2 or more, structures in parentheses may be the same or different.

In Formula 4, in a case where q is 1, L₅ may be a monovalent group, in acase where q is 2, L₅ may be a divalent group, and in a case where q is3, L₅ may be a trivalent group.

In an implementation, in Formula 4, q may be 2, and L₅ may be, e.g., asubstituted or unsubstituted arylene group having 6 to 15 ring carbonatoms. In an implementation, in Formula 4, q may be 2, and L₅ may be,e.g., a substituted or unsubstituted monocyclic arylene group. In animplementation, in Formula 4, q may be 2, and L₅ may be a substituted orunsubstituted phenylene group, e.g., an m-phenylene group. Formula 4corresponds to Formula 1 where R₂ is a group represented by -L₁-Y₁.

In an implementation, in Formula 4, X may be, e.g., NR₅.

In an implementation, in Formula 4, at least one of R₁ to R₃ may be,e.g., a substituted or unsubstituted silyl group. In an implementation,in Formula 4, at least two of R₁ to R₃ may not be an aryl group or aheteroaryl group.

As described above, in an implementation, in Formula 1, R₁ to R₄ mayform a ring via the combination of adjacent groups with each other. Inan implementation, in Formula 1, adjacent groups of R₁ to R₄ may becombined with each other to form a substituted or unsubstitutedhydrocarbon ring, or a substituted or unsubstituted heterocycle. In animplementation, the compound represented by Formula 1 may be representedby Formula 5 below.

In Formula 5, W may be, e.g., O, S, PR₈, S═O, SO₂, P═OR₉, CR₁₀R₁₁, orSiR₁₂R₁₃. R₆ to R₁₃ may each independently be or include, e.g., ahydrogen atom, a deuterium atom, a substituted or unsubstituted alkylgroup having 1 to 10 carbon atoms, a substituted or unsubstituted arylgroup having 6 to 30 ring carbon atoms, or a substituted orunsubstituted heteroaryl group having 2 to 30 ring carbon atoms, a and bmay each independently be, e.g., an integer of 0 to 4. X, R₁ and R₄ maybe the same as described above.

In a case where a is 2 or more, a plurality of R₆ may be the same ordifferent. In a case where b is 2 or more, a plurality of R₇ may be thesame or different.

In an implementation, in Formula 5, W may be, e.g., O or CR₁₀R₁₁.

In an implementation, in Formula 5, at least one of R₁ to R₄ may be,e.g., a substituted or unsubstituted silyl group, a substituted orunsubstituted alkoxy group, a substituted or unsubstituted aryloxygroup, a substituted or unsubstituted alkythio group, a substituted orunsubstituted arylthio group, a substituted or unsubstituted borylgroup, a substituted or unsubstituted aralkyl group, a substituted orunsubstituted sulfoxy group, or a substituted or unsubstituted phosphineoxide group.

In an implementation, in Formula 5, at least one of R₁ and R₄ may be,e.g., a substituted or unsubstituted silyl group. In an implementation,in Formula 5, at least one of R₁ and R₄ may be, e.g., a substituted orunsubstituted triphenylsilyl group.

In an implementation, the compound represented by Formula 1 may berepresented by Formula 6 below.

In Formula 6, W, R₆, R₇, a, and b may be the same as defined in Formula5, and R₃, R₄, and X are the same as defined above.

In an implementation, the compound represented by Formula 1 may berepresented by Formula 7 below.

In Formula 7, Cy1 and Cy2 may each independently be or include, e.g., asubstituted or unsubstituted hydrocarbon ring or a substituted orunsubstituted heterocycle. The hydrocarbon ring may include an aromatichydrocarbon ring and an aliphatic hydrocarbon ring, and the heterocyclemay include an aromatic heterocycle and an aliphatic heterocycle. In animplementation, Cy1 and Cy2 may each independently be a five-memberedring or a six-membered ring.

In Formula 7, W may be the same as defined in Formula 5, and R₁, R₄, andX may be the same as defined in Formula 1.

The heterocyclic compound represented by Formula 1 may be used as amaterial for an organic electroluminescence device. For example, theheterocyclic compound represented by Formula 1 may be used as a holetransport material.

In an implementation, the heterocyclic compound represented by Formula 1may be, e.g., a compound of the following Compound Group 1.

When the heterocyclic compound according to an embodiment of the presentdisclosure is used in an organic electroluminescence device, effects ofhigh efficiency and/or long life may be achieved.

Hereinafter, an organic electroluminescence device according to anembodiment of the inventive step will be explained. The explanation willbe mainly with the difference in the heterocyclic compound according toan embodiment of the present disclosure, and unexplained part willfollow the above-description on the heterocyclic compound according toan embodiment of the present disclosure.

The organic electroluminescence device according to an embodiment of thepresent disclosure may include the above-described heterocycliccompound.

FIG. 1 illustrates a cross-sectional view of an organicelectroluminescence device according to an embodiment of the presentdisclosure. FIG. 2 illustrates a cross-sectional view of an organicelectroluminescence device according to an embodiment of the presentdisclosure.

Referring to FIGS. 1 and 2, an organic electroluminescence device 10according to an embodiment of the present disclosure may include a firstelectrode EL1, a hole transport region HTR, an emission layer EML, anelectron transport region ETR, and a second electrode EL2.

The first electrode EL1 has conductivity. The first electrode EL1 may bea pixel electrode or an anode. The first electrode EL1 may be atransmissive electrode, a transflective electrode, or a reflectiveelectrode. In a case where the first electrode EL1 is the transmissiveelectrode, the first electrode EL1 may be formed using a transparentmetal oxide such as indium tin oxide (ITO), indium zinc oxide (IZO),zinc oxide (ZnO), or indium tin zinc oxide (ITZO). In a case where thefirst electrode EL1 is the transflective electrode or reflectiveelectrode, the first electrode EL1 may include Ag, Mg, Cu, Al, Pt, Pd,Au, Ni, Nd, Ir, Cr, Li, Ca, LiF/Ca, LiF/Al, Mo, Ti, a compound thereof,or a mixture thereof (for example, a mixture of Ag and Mg). Also, thefirst electrode EL1 may include a plurality of layers including thereflective layer or transflective layer formed using the abovematerials, or a transparent layer formed using ITO, IZO, ZnO, or ITZO.

The hole transport region HTR is provided on the first electrode EL1.The hole transport region HTR may include at least one of a holeinjection layer HIL, a hole transport layer HTL, a hole buffer layer, oran electron blocking layer. The thickness of the hole transport regionHTR may be, e.g., from about 1.000 Å to about 1,500 Å.

Hereinafter, an embodiment of including the heterocyclic compound in ahole transport region HTR will be explained. In an implementation, theheterocyclic compound according to an embodiment of the presentdisclosure may be included in at least one organic layer providedbetween a first electrode EL1 and a second electrode EL2. For example,the heterocyclic compound according to an embodiment of the presentdisclosure may be included in an emission layer EML.

The hole transport region HTR may include the heterocyclic compoundaccording to an embodiment of the present disclosure. For example, thehole transport region HTR may include a heterocyclic compoundrepresented by Formula 1.

Particular description on X and R₁ to R₄ are the same as described aboveand will be omitted. For example, X may be NR₅.

The hole transport region HTR may have a single layer formed using asingle material, a single layer formed using a plurality of differentmaterials, or a multilayer structure including a plurality of layersformed using a plurality of different materials.

For example, the hole transport region HTR may have the structure of asingle layer such as a hole injection layer HIL and a hole transportlayer HTL, or may have a structure of a single layer formed using a holeinjection material and a hole transport material. In an implementation,the hole transport region HTR may have a structure of a single layerformed using a plurality of different materials, or a structurelaminated one by one from the first electrode EL1 of hole injectionlayer HIL/hole transport layer HTL, hole injection layer HIL/holetransport layer HTL/hole buffer layer, hole injection layer HIL/holebuffer layer, hole transport layer HTL/hole buffer layer, or holeinjection layer HIL/hole transport layer HTL/electron blocking layer.

In a case where the hole transport region HTR includes a structure ofhole injection layer HIL/hole transport layer HTL, the heterocycliccompound according to an embodiment of the present disclosure may beincluded in the hole transport layer HTL. In an implementation, when thehole transport region HTR has a multilayer structure, the heterocycliccompound according to an embodiment of the present disclosure may beincluded in a layer contacting an emission layer, or in each of thelayer contacting an emission layer and the hole transport layer HTR.When the hole transport layer HTL includes the heterocyclic compoundaccording to an embodiment of the present disclosure, the hole transportlayer HTL may include one kind or two or more kinds of the heterocycliccompound.

The hole transport region HTR may be formed using various methods suchas a vacuum deposition method, a spin coating method, a cast method, aLangmuir-Blodgett (LB) method, an inkjet printing method, a laserprinting method, and a laser induced thermal imaging (LITI) method.

The hole injection layer HIL may include, e.g., a phthalocyaninecompound such as copper phthalocyanine;N,N′-diphenyl-N,N′-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4′-diamine(DNTPD), 4,4′,4″-tris(3-methylphenylphenylamino)triphenylamine(m-MTDATA), 4,4′,4″-tris(N,N-diphenylamino)triphenylamine (TDATA),4,4′,4″-tris {N-(2-naphthyl)-N-phenylamino}-triphenylamine (2-TNATA),poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS),polyaniline/dodecylbenzenesulfonic acid (PANI/DBSA), polyaniline/camphorsulfonic acid (PANI/CSA), polyaniline/poly(4-styrenesulfonate)(PANI/PSS), N,N′-dinaphthalene-1-yl)-N,N′-diphenyl-benzidine (NPB),triphenylamine-containing polyether ketone (TPAPEK),4-isopropyl-4′-methyldiphenyliodonium tetrakis(pentafluorophenyl)borate,dipyrazino[2,3-f: 2′,3′-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile(HAT-CN), etc.

When the hole transport layer HTL includes the heterocyclic compoundaccording to an embodiment of the present disclosure, other materialsmay be further include in addition to the heterocyclic compound. Forexample, carbazole derivatives such as N-phenyl carbazole and polyvinylcarbazole, fluorine-based derivatives,N,N′-bis(3-methylphenyl)-N,N′-diphenyl-[1,1-biphenyl]-4,4′-diamine(TPD), triphenylamine-based derivatives such as4,4′,4″-tris(N-carbazolyl)triphenylamine (TCTA),N,N′-di(1-naphthyl)-N,N′-diphenylbenzidine (NPB), 4,4′-cyclohexylidenebis[N,N-bis(4-methylphenyl)benzenamine] (TAPC),4,4′-bis[N,N′-(3-tolyl)amino]-3,3′-dimethylbiphenyl (HMTPD), etc. may befurther included.

The thickness of the hole transport region HTR may be from about 100 Åto about 10,000 Å, e.g., from about 100 Å to about 1,000 Å. In a casewhere the hole transport region HTR includes both the hole injectionlayer HIL and the hole transport layer HTL, the thickness of the holeinjection layer HIL may be from about 100 Å to about 10,000 Å, e.g.,from about 100 Å to about 1,000 Å, and the thickness of the holetransport layer HTL may be from about 30 Å to about 1,000 Å. In a casewhere the thicknesses of the hole transport region HTR, the holeinjection layer HIL, and the hole transport layer HTL satisfy theabove-described ranges, satisfactory hole transport properties may beobtained without the substantial increase of a driving voltage.

The hole transport region HTR may further include a charge generatingmaterial other than the above-described materials to improveconductivity. The charge generating material may be dispersed in thehole transport region HTR uniformly or non-uniformly. The chargegenerating material may be, for example, a p-dopant. The p-dopant may beone of quinone derivatives, metal oxides, or cyano group-containingcompounds. Examples of the p-dopant may include quinone derivatives suchas Tetracyanoquinodimethane (TCNQ), and2,3,5,6-tetrafluoro-tetracyanoquinodimethane (F4-TCNQ), and metal oxidessuch as tungsten oxide, and molybdenum oxide.

As described above, the hole transport region HTR may further includeone of a hole buffer layer or an electron blocking layer other than thehole injection layer HIL and the hole transport layer HTL. The holebuffer layer may compensate an optical resonance distance according tothe wavelength of light emitted from the emission layer EML and increaselight emission efficiency. Materials included in the hole transportregion HTR may be used as materials included in the hole buffer layer.The electron blocking layer is a layer preventing electron injectionfrom the electron transport region ETR to the hole transport region HTR.

The emission layer EML is provided on the hole transport region HTR. Theemission layer EML is a layer emitting light by fluorescence orphosphorescence and may be formed to a thickness of about 100 Å to about600 Å.

The emission layer EML may have a single layer formed using a singlematerial, a single layer formed using a plurality of differentmaterials, or a multilayer structure having a plurality of layers formedusing a plurality of different materials.

As the material of the emission layer EML, known emission materials maybe used and may be selected from fluoranthene derivatives, pyrenederivatives, arylaceylene derivatives, fluorene derivatives, perylenederivatives, chrysene derivatives, or the like. For example, pyrenederivatives, perylene derivatives, and anthracene derivatives may beused.

For example, the emission layer EML may include a fluorescent materialincluding spiro-DPVBi,2,2′,7,7′-tetrakis(biphenyl-4-yl)-9,9′-spirobifluorene (spiro-6P,spiro-sexiphenyl), distyryl-benzene (DSB), distyryl-arylene (DSA), apolyfluorene (PFO)-based polymer, and a poly(p-phenylene vinylene)(PPV)-based polymer.

The emission layer may further include a dopant and the dopant may useknown materials. For example, styryl derivatives (for example,1,4-bis[2-(3-N-ethylcarbazoryl)vinyl]benzene (BCzVB),4-(di-p-tolylamino)-4″-[(di-p-tolylamino)styryl]stilbene (DPAVB),N-(4-((E)-2-(6-((E)-4-(diphenylamino)styryl)naphthalen-2-yl)vinyl)phenyl)-N-phenylbenzenamine(N-BDAVBi)), perylene and the derivatives thereof (for example,2,5,8,11-tetra-t-butylperylene (TBPe)), pyrene and the derivativesthereof (for example, 1,1-dipyrene. 1,4-dipyrenylbenzene,1,4-bis(N,N-diphenylamino)pyrene), 2,5,8,11-tetra-t-butylperylene (TBP),1,3,5-tris(N-phenylbenzimidazole-2-yl)benzene (TPBi), orbis[2(4,5-difluorophenyl)pyridinato-C²,N](picolinato) (Firpic), or thelike may be used as the dopant.

The emission layer EML may include, e.g.,tris(8-hydroxyquinolino)aluminum (Alq3),4,4′-bis(N-carbazolyl)-1,1′-biphenyl (CBP), poly(n-vinylcarbazole)(PVK), 9,10-di(naphthalene-2-yl)anthracene (ADN),4,4′,4″-tris(carbazol-9-yl)-triphenylamine (TCTA),1,3,5-tris(N-phenylbenzimidazole-2-yl)benzene (TPBi),3-tert-butyl-9,10-di(naphth-2-yl)anthracene (TBADN), distyrylarylene(DSA), 4,4′-bis(9-carbazolyl)-2,2′-dimethyl-biphenyl (CDBP),2-methyl-9,10-bis(naphthalen-2-yl)anthracene (MADN),bis[2-(diphenylphosphino)phenyl] ether oxide (DPEPO), hexaphenylcyclotriphosphazene (CP1), 1,4-bis(triphenylsilyl)benzene (UGH2),hexaphenylcyclotrisiloxane (DPSiO3), octaphenylcyclotetra siloxane(DPSiO₄), 1,3-bis(N-carbazolyl)benzene (mCP),2,8-bis(diphenylphosphoryl)dibenzofuran (PPF), etc.

The electron transport region ETR is provided on the emission layer EML.The electron transport region ETR may include, e.g., at least one of anelectron blocking layer, an electron transport layer ETL, or an electroninjection layer EIL.

The electron transport region ETR may have a single layer formed using asingle material, a single layer formed using a plurality of differentmaterials, or a multilayer structure including a plurality of layersformed using a plurality of different materials.

For example, the electron transport region ETR may have the structure ofa single layer such as the electron injection layer EIL or the electrontransport layer ETL, or a single layer structure formed using anelectron injection material and an electron transport material. In animplementation, the electron transport region ETR may have a singlelayer structure formed using a plurality of different materials, or astructure laminated one by one from the first electrode EL1 of electrontransport layer ETL/electron injection layer EIL, or hole blockinglayer/electron transport layer ETL/electron injection layer EIL. Thethickness of the electron transport region ETR may be, e.g., from about1,000 Å to about 1,500 Å.

The electron transport region ETR may be formed using various methodssuch as a vacuum deposition method, a spin coating method, a castmethod, a Langmuir-Blodgett (LB) method, an inkjet printing method, alaser printing method, and a laser induced thermal imaging (LITI)method.

In a case where the electron transport region ETR includes the electrontransport layer ETL, the electron transport region ETR may includetris(8-hydroxyquinolinato)aluminum (Alq₃),1,3,5-tri[(3-pyridyl)-phen-3-yl]benzene,2,4,6-tris(3′-(pyridin-3-yl)biphenyl-3-yl)-1,3,5-triazine,2-(4-(N-phenylbenzoimidazolyl-1-ylphenyl)-9,10-dinaphthylanthracene,1,3,5-tri(1-phenyl-1H-benzo[d]imidazol-2-yl)phenyl (TPBi),2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP),4,7-diphenyl-1,10-phenanthroline (Bphen),3-(4-biphenylyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ),4-(naphthalen-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ),2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (tBu-PBD),bis(2-methyl-8-quinolinolato-N1,O8)-(1,1′-biphenyl-4-olato)aluminum(BAlq), berylliumbis(benzoquinolin-10-olate (Bebq2),9,10-di(naphthalene-2-yl)anthracene (ADN), or a mixture thereof. Thethickness of the electron transport layer ETL may be from about 100 Å toabout 1,000 Å, e.g., from about 150 Å to about 500 Å. If the thicknessof the electron transport layer ETL satisfies the above-described range,satisfactory electron transport properties may be obtained without thesubstantial increase of a driving voltage.

In a case where the electron transport region ETR includes the electroninjection layer EIL, the electron transport region ETR may include LiF,lithium quinolate (LiQ), Li₂O, BaO, NaCl, CsF, a metal in lanthanidessuch as Yb, or a metal halide such as RbCl and RbI. The electroninjection layer EIL also may be formed using a mixture material of anelectron transport material and an insulating organo metal salt. Theorgano metal salt may be a material having an energy band gap of about 4eV or more. Particularly, the organo metal salt may include, forexample, a metal acetate, a metal benzoate, a metal acetoacetate, ametal acetylacetonate, or a metal stearate. The thickness of theelectron injection layer EIL may be from about 1 Å to about 100 Å, e.g.,about 3 Å to about 90 Å. In a case where the thickness of the electroninjection layer EIL satisfies the above described range, satisfactoryelectron injection properties may be obtained without inducing thesubstantial increase of a driving voltage.

The electron transport region ETR may include a hole blocking layer, asdescribed above. The hole blocking layer may include, e.g., at least oneof 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), or4,7-diphenyl-1,10-phenanthroline (Bphen).

The second electrode EL2 is provided on the electron transport regionETR. The second electrode EL2 may be a common electrode or a cathode.The second electrode EL2 may be a transmissive electrode, atransflective electrode or a reflective electrode. In a case where thesecond electrode EL2 is the transmissive electrode, the second electrodeEL2 may include a transparent metal oxide, e.g., ITO, IZO, ZnO, ITZO,etc.

In a case where the second electrode EL2 is the transflective electrodeor the reflective electrode, the second electrode EL2 may include Ag,Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF/Ca, LiF/Al, Mo, Ti,a compound including thereof, or a mixture thereof (for example, amixture of Ag and Mg). The second electrode EL2 may have a multilayeredstructure including a reflective layer or a transflective layer formedusing the above-described materials or a transparent conductive layerformed using ITO, IZO, ZnO, ITZO, etc.

In an implementation, the second electrode EL2 may be connected with anauxiliary electrode. If the second electrode EL2 is connected with theauxiliary electrode, the resistance of the second electrode EL2 may bedecreased.

In the organic electroluminescence device 10, voltages are applied toeach of the first electrode EL1 and the second electrode EL2, and holesinjected from the first electrode EL1 move via the hole transport regionHTR to the emission layer EML, and electrons injected from the secondelectrode EL2 move via the electron transport region ETR to the emissionlayer EML. The electrons and holes are recombined in the emission layerEML to generate excitons, and the excitons may emit light via transitionfrom an excited state to a ground state.

The organic electroluminescence device according to an embodiment of thepresent disclosure includes the heterocyclic compound represented byFormula 1 and may accomplish high efficiency and/or long life.

Hereinafter, the present disclosure will be explained more particularlyreferring to preferred embodiments and comparative embodiments. Thefollowing embodiments are only for illustration to assist theunderstanding of the present disclosure, but the scope of the presentdisclosure is not limited thereto.

The following Examples and Comparative Examples are provided in order tohighlight characteristics of one or more embodiments, but it will beunderstood that the Examples and Comparative Examples are not to beconstrued as limiting the scope of the embodiments, nor are theComparative Examples to be construed as being outside the scope of theembodiments. Further, it will be understood that the embodiments are notlimited to the particular details described in the Examples andComparative Examples.

Synthetic Examples

The heterocyclic compound according to an embodiment of the presentdisclosure may be synthesized, e.g., as follows.

1. Synthesis of Compound 1

Compound 1 was synthesized by the following reaction:

Under an argon (Ar) atmosphere, 80 ml of a dehydrated THF solution of6.3 ml of 2,2,6,6-tetramethylpiperidine was added to a 500 ml three neckflask, and 23 ml (36.8 mmol) of a hexane solution of 1.6 M n-BuLi wasadded thereto dropwise at about 0° C., followed by stirring for about 2hours. The temperature was decreased to about −78° C. and 92 ml of a THFsolution of 5.43 g (18.4 mmol) of Compound A was added thereto, followedby stirring at about −78° C. for about 2 hours. Then, 80 ml of adehydrated THF solution of 10.85 g (36.8 mmol) of chlorotriphenylsilanewas added thereto dropwise and stirred for about 2 hours, followed bystirring at ambient temperature for about 3 hours. After finishing thereaction, 1N HCl aqueous solution was added and stirred for about 1hour. The solution thus obtained was washed with water, and an organicphase was concentrated to obtain a viscous material. The crude productthus obtained was separated by silica gel column chromatography toproduce 6.72 g (yield 45%) of Compound 1 as a white solid.

The molecular weight of Compound 1 measured by FAB-MS was 812. Thechemical shift values (δ) of Compound 1 measured by ¹H NMR (CDCl₃) wereas follows. ¹H-NMR (300 MHz, CDCl₃): 7.63-7.57 (3H), 7.52-7.45 (22H),7.42-7.37 (20H).

2. Synthesis of Compound 3

Under an argon (Ar) atmosphere, 80 ml of a dehydrated THF solution of6.3 ml of 2,2,6,6-tetramethylpiperidine was added to a 500 ml three neckflask, and 23 ml (36.8 mmol) of a hexane solution of 1.6 M n-BuLi wasadded thereto dropwise at about 0° C., followed by stirring for about 2hours. The temperature was decreased to about −78° C. and 92 ml of adehydrated THF solution of 5.43 g (18.4 mmol) of Compound B was addedthereto, followed by stirring at about −78° C. for about 2 hours. Then,80 ml of a dehydrated THF solution of 10.85 g (36.8 mmol) ofchlorotriphenylsilane was added thereto dropwise and stirred for about 2hours, followed by stirring at ambient temperature for about 3 hours.After finishing the reaction, 1N HCl aqueous solution was added andstirred for about 1 hour. The solution thus obtained was washed withwater, and an organic phase was concentrated to obtain a viscousmaterial. The crude product thus obtained was separated by silica gelcolumn chromatography to produce 5.08 g (yield 34%) of Compound 3 as awhite solid.

The molecular weight of Compound 1 measured by FAB-MS was 812. Thechemical shift values (δ) of Compound 3 measured by ¹H NMR (CDCl₃) wereas follows. ¹H-NMR (CDCl₃): 7.84 (4H), 7.63-7.57 (3H), 7.54-7.45 (20H),7.39-7.37 (18H).

3. Synthesis of Compound 11

Under an argon (Ar) atmosphere, 100 ml of a dehydrated THF solution of7.7 ml of 2,2,6,6-tetramethylpiperidine was added to a 500 ml three neckflask, and 28 ml (45.0 mmol) of a hexane solution of 1.6 M n-BuLi wasadded thereto dropwise at about 0° C., followed by stirring for about 2hours. The temperature was decreased to about −78° C. and 113 ml of adehydrated THF solution of 4.96 g (22.5 mmol) of Compound C was addedthereto, followed by stirring at about −78° C. for about 2 hours. Then,100 ml of a dehydrated THF solution of 13.27 g (45.0 mmol) ofchlorotriphenylsilane was added thereto dropwise and stirred for about 2hours, followed by stirring at ambient temperature for about 3 hours.After finishing the reaction, 1N HCl aqueous solution was added andstirred for about 1 hour. The solution thus obtained was washed withwater, and an organic phase was concentrated to obtain a viscousmaterial. The crude product thus obtained was separated by silica gelcolumn chromatography to produce 8.62 g (yield 52%) of Compound 11 as awhite solid.

The molecular weight of Compound 11 measured by FAB-MS was 737. Thechemical shift values (δ) of Compound 11 measured by ¹H NMR (CDCl₃) wereas follows. ¹H-NMR (CDCl₃): 7.52-7.45 (20H), 7.42-7.37 (20H).

4. Synthesis of Compound 13

Under an argon (Ar) atmosphere, 100 ml of a dehydrated THF solution of7.7 ml of 2,2,6,6-tetramethylpiperidine was added to a 500 ml three neckflask, and 28 ml (45.0 mmol) of a hexane solution of 1.6 M n-BuLi wasadded thereto dropwise at about 0° C., followed by stirring for about 2hours. The temperature was decreased to about −78° C. and 113 ml of adehydrated THF solution of 4.96 g (22.5 mmol) of Compound C was addedthereto, followed by stirring at about −78° C. for about 2 hours. Then,100 ml of a dehydrated THF solution of 13.27 g (45.0 mmol) ofchlorotriphenylsilane was added thereto dropwise and stirred for about 2hours, followed by stirring at ambient temperature for about 3 hours.After finishing the reaction, 1N HCl aqueous solution was added andstirred for about 1 hour. The solution thus obtained was washed withwater, and an organic phase was concentrated to obtain a viscousmaterial. The crude product thus obtained was separated by silica gelcolumn chromatography to produce 6.47 g (yield 39%) of Compound 13 as awhite solid.

The molecular weight of Compound 13 measured by FAB-MS was 737. Thechemical shift values (δ) of Compound 13 measured by ¹H NMR (CDCl₃) wereas follows. ¹H-NMR (CDCl₃): 8.07 (4H), 7.61-7.59 (6H), 7.46 (12H),7.39-7.37 (18H).

Device Manufacturing Examples

Organic electroluminescence devices of Examples 1 to 4 were manufacturedusing Compounds 1, 3, 11, and 13 as hole transport materials.

Example Compounds

Organic electroluminescence devices of Comparative Examples 1 to 5 weremanufactured using Comparative Compounds c1 to c5 as hole transportmaterials.

Comparative Compounds

TABLE 1 Device manufacturing Maximum example Hole transport materialemission life Example 1 Example Compound 1 115% Example 2 ExampleCompound 3 125% Example 3 Example Compound 11 115% Example 4 ExampleCompound 13 105% Comparative Example 1 Comparative Compound c1 100%Comparative Example 2 Comparative Compound c2  95% Comparative Example 3Comparative Compound c3  90% Comparative Example 4 Comparative Compoundc4 100% Comparative Example 5 Comparative Compound c5 100%

The emission efficiency of the devices were respectively measured usingSource Meter of 2400 Series manufactured by Keithley Instruments Co.Ltd., a CS-200 Chroma Meter manufactured by Konica Minolta Holdings Co.Ltd., and PC program LabVIEW 8.2 for measurement manufactured byJapanese National Instruments Co., Ltd. in a dark room.

From the results of Table 1, the heterocyclic compound of Examples 1-4exhibited an effect of improving the emission efficiency of an organicelectroluminescence device.

For example, the heterocyclic compound of Examples 1-4 included amonocyclic group such as pyrrole, furan, or thiophene as a mainskeleton, and had good hole transport properties and a high triplet (T1)energy level (or high energy gap). By using the heterocyclic compound ina hole transport layer which is adjacent to an emission layer, theemission efficiency of an organic electroluminescence device may beimproved. Examples 1 to 4 had a higher triplet (T1) energy level thanComparative Examples 1 to 5, and emission efficiency was improved.

The heterocyclic compound according to an embodiment of the presentdisclosure has excellent emission efficiency.

The organic electroluminescence device including the heterocycliccompound according to an embodiment of the present disclosure mayaccomplish high emission efficiency

The embodiments may provide a heterocyclic compound which may be used asa hole transport material and an organic electroluminescence deviceincluding the same in a hole transport region.

Example embodiments have been disclosed herein, and although specificterms are employed, they are used and are to be interpreted in a genericand descriptive sense only and not for purpose of limitation. In someinstances, as would be apparent to one of ordinary skill in the art asof the filing of the present application, features, characteristics,and/or elements described in connection with a particular embodiment maybe used singly or in combination with features, characteristics, and/orelements described in connection with other embodiments unless otherwisespecifically indicated. Accordingly, it will be understood by those ofskill in the art that various changes in form and details may be madewithout departing from the spirit and scope of the present invention asset forth in the following claims.

What is claimed is:
 1. A heterocyclic compound represented by thefollowing Formula 1:

Wherein in Formula 1, X is NR₅, O, or S, R₁ to R₄ are each independentlya hydrogen atom, a substituted or unsubstituted amino group, asubstituted or unsubstituted silyl group, a substituted or unsubstitutedalkoxy group, a substituted or unsubstituted aryloxy group, asubstituted or unsubstituted alkythio group, a substituted orunsubstituted arylthio group, a substituted or unsubstituted borylgroup, a substituted or unsubstituted sulfoxy group, a substituted orunsubstituted phosphine oxide group, a substituted or unsubstitutedcarbonyl group, a substituted or unsubstituted alkyl group having 1 to10 carbon atoms, a substituted or unsubstituted aralkyl group, asubstituted or unsubstituted aryl group having 6 to 30 ring carbonatoms, or a substituted or unsubstituted heteroaryl group having 2 to 30ring carbon atoms, R₁ to R₄ being separate or forming a ring viacombination of adjacent groups with each other, R₅ is a hydrogen atom, adeuterium atom, a substituted or unsubstituted silyl group, asubstituted or unsubstituted boryl group, a substituted or unsubstitutedsulfoxy group, a substituted or unsubstituted phosphine oxide group, asubstituted or unsubstituted carbonyl group, a substituted orunsubstituted alkyl group having 1 to 10 carbon atoms, a substituted orunsubstituted aralkyl group, a substituted or unsubstituted aryl grouphaving 6 to 30 ring carbon atoms, or a substituted or unsubstitutedheteroaryl group having 2 to 30 ring carbon atoms, at least one of R₁ toR₄ is a substituted or unsubstituted silyl group, a substituted orunsubstituted alkoxy group, a substituted or unsubstituted aryloxygroup, a substituted or unsubstituted alkythio group, a substituted orunsubstituted arylthio group, a substituted or unsubstituted borylgroup, a substituted or unsubstituted aralkyl group, a substituted orunsubstituted sulfoxy group, or a substituted or unsubstituted phosphineoxide group, and at least two of R₁ to R₄ are not an aryl group or aheteroaryl group.
 2. The heterocyclic compound as claimed in claim 1,wherein: two of R₁ to R₄ are each independently an aryl group or aheteroaryl group, and at least one of the remaining ones of R₁ to R₄ isa substituted or unsubstituted silyl group, a substituted orunsubstituted alkoxy group, a substituted or unsubstituted aryloxygroup, a substituted or unsubstituted alkythio group, a substituted orunsubstituted arylthio group, a substituted or unsubstituted borylgroup, a substituted or unsubstituted aralkyl group, a substituted orunsubstituted sulfoxy group, or a substituted or unsubstituted phosphineoxide group.
 3. The heterocyclic compound as claimed in claim 1,wherein: two of R₁ to R₄ are each independently a substituted orunsubstituted aryl group having 6 to 15 ring carbon atoms or asubstituted or unsubstituted heteroaryl group having 2 to 15 ring carbonatoms, and at least one of the remaining ones of R₁ to R₄ is asubstituted or unsubstituted silyl group.
 4. The heterocyclic compoundas claimed in claim 3, wherein: two of R₁ to R₄ are each independently asubstituted or unsubstituted phenyl group, and at least one of theremaining ones of R₁ to R₄ is a triphenylsilyl group.
 5. Theheterocyclic compound as claimed in claim 1, wherein X is NR₅.
 6. Theheterocyclic compound as claimed in claim 5, wherein R₅ is a substitutedor unsubstituted aryl group having 6 to 15 ring carbon atoms.
 7. Theheterocyclic compound as claimed in claim 5, wherein R₅ is a substitutedor unsubstituted phenyl group.
 8. The heterocyclic compound as claimedin claim 1, wherein: X is NR₅, at least one of R₁ to R₅ is a grouprepresented by -L₁-Y₁, L₁ is a substituted or unsubstituted arylenegroup having 6 to 30 ring carbon atoms, and Y₁ is a substituted orunsubstituted silyl group, a substituted or unsubstituted pyrrolylgroup, a substituted or unsubstituted thienyl group, or a substituted orunsubstituted furanyl group.
 9. The heterocyclic compound as claimed inclaim 1, wherein the compound represented by Formula 1 is represented bythe following Formula 2:

wherein in Formula 2, n is an integer of 1 to 3, when n is 2 or 3, aplurality of R₁ to R₄ are the same or different from each other, L₃ is adirect linkage or a substituted or unsubstituted aryl group having 6 to30 ring carbon atoms, and R₁ to R₄ are defined the same as those ofFormula
 1. 10. The heterocyclic compound as claimed in claim 1, whereinthe compound represented by Formula 1 is represented by the followingFormula 3:

wherein in Formula 3, m is an integer of 1 to 3, when m is 2 or 3, aplurality of R₁, R₂, and R₄ are the same or different from each other,L₄ is a direct linkage or a substituted or unsubstituted aryl grouphaving 6 to 30 ring carbon atoms, and X, R₁, R₂, and R₄ are defined thesame as those of Formula
 1. 11. The heterocyclic compound as claimed inclaim 1, wherein the compound represented by Formula 1 is represented bythe following Formula 4:

wherein in Formula 4, q is an integer of 1 to 3, when q is 2 or 3, aplurality of R₁ to R₃ are the same or different from each other, L₅ is adirect linkage or a substituted or unsubstituted aryl group having 6 to30 ring carbon atoms, and X, and R₁ to R₃ are defined the same as thoseof Formula
 1. 12. The heterocyclic compound as claimed in claim 1,wherein the compound represented by Formula 1 is represented by thefollowing Formula 5:

wherein Formula 5, W is O, S, PR₈, S═O, SO₂, P═OR₉, CR₁₀R₁₁, orSiR₁₂R₁₃, R₆ to R₁₃ are each independently a hydrogen atom, a deuteriumatom, a substituted or unsubstituted alkyl group having 1 to 10 carbonatoms, a substituted or unsubstituted aryl group having 6 to 30 ringcarbon atoms, or a substituted or unsubstituted heteroaryl group having2 to 30 ring carbon atoms, a and b are each independently an integer of0 to 4, and X, R₁ and R₄ are defined the same as those of Formula
 1. 13.The heterocyclic compound as claimed in claim 1, wherein theheterocyclic compound represented by Formula 1 is a compound of thefollowing Compound Group 1:


14. An organic electroluminescence device, comprising: a firstelectrode; a hole transport region on the first electrode; an emissionlayer on the hole transport region; an electron transport region on theemission layer; and a second electrode on the electron transport region,wherein the hole transport region includes a heterocyclic compoundrepresented by the following Formula 1:

wherein in Formula 1, X is NR₅, O or S, R₁ to R₄ are each independentlya hydrogen atom, a substituted or unsubstituted amino group, asubstituted or unsubstituted silyl group, a substituted or unsubstitutedalkoxy group, a substituted or unsubstituted aryloxy group, asubstituted or unsubstituted alkythio group, a substituted orunsubstituted arylthio group, a substituted or unsubstituted borylgroup, a substituted or unsubstituted sulfoxy group, a substituted orunsubstituted phosphine oxide group, a substituted or unsubstitutedcarbonyl group, a substituted or unsubstituted alkyl group having 1 to10 carbon atoms, a substituted or unsubstituted aralkyl group, asubstituted or unsubstituted aryl group having 6 to 30 ring carbonatoms, or a substituted or unsubstituted heteroaryl group having 2 to 30ring carbon atoms, R₁ to R₄ being separate or forming a ring viacombination of adjacent groups with each other, R₅ is a hydrogen atom, adeuterium atom, a substituted or unsubstituted silyl group, asubstituted or unsubstituted boryl group, a substituted or unsubstitutedsulfoxy group, a substituted or unsubstituted phosphine oxide group, asubstituted or unsubstituted carbonyl group, a substituted orunsubstituted alkyl group having 1 to 10 carbon atoms, a substituted orunsubstituted aralkyl group, a substituted or unsubstituted aryl grouphaving 6 to 30 ring carbon atoms, or a substituted or unsubstitutedheteroaryl group having 2 to 30 ring carbon atoms, at least one of R₁ toR₄ is a substituted or unsubstituted silyl group, a substituted orunsubstituted alkoxy group, a substituted or unsubstituted aryloxygroup, a substituted or unsubstituted alkythio group, a substituted orunsubstituted arylthio group, a substituted or unsubstituted borylgroup, a substituted or unsubstituted aralkyl group, a substituted orunsubstituted sulfoxy group, or a substituted or unsubstituted phosphineoxide group, and at least two of R₁ to R₄ are not an aryl group or aheteroaryl group.
 15. The organic electroluminescence device as claimedin claim 14, wherein: two of R₁ to R₄ are each independently an arylgroup or a heteroaryl group, and at least one of the remaining ones ofR₁ to R₄ is a substituted or unsubstituted silyl group, a substituted orunsubstituted alkoxy group, a substituted or unsubstituted aryloxygroup, a substituted or unsubstituted alkythio group, a substituted orunsubstituted arylthio group, a substituted or unsubstituted borylgroup, a substituted or unsubstituted aralkyl group, a substituted orunsubstituted sulfoxy group, or a substituted or unsubstituted phosphineoxide group.
 16. The organic electroluminescence device as claimed inclaim 14, wherein X is NR₅, at least one of R₁ to R₅ is a grouprepresented by -L₁-Y₁, L₁ is a substituted or unsubstituted arylenegroup having 6 to 30 ring carbon atoms, and Y₁ is a substituted orunsubstituted silyl group, a substituted or unsubstituted pyrrolylgroup, a substituted or unsubstituted thienyl group, or a substituted orunsubstituted furanyl group.
 17. The organic electroluminescence deviceas claimed in claim 14, wherein X is NR₅, and R₅ is the same as definedin claim
 14. 18. The organic electroluminescence device as claimed inclaim 14, wherein the compound represented by Formula 1 is representedby one of the following Formulae 2 to 4:

wherein in Formulae 2 to 4, n, m, and p are each independently aninteger of 1 to 3, when n is 2 or 3, a plurality of R₁ to R₄ are thesame or different from each other, when m is 2 or 3, a plurality of R₁,R₂, and R₄ are the same or different from each other, when q is 2 or 3,a plurality of R₁ to R₃ are the same or different from each other, L₃ toL₅ are each independently a direct linkage or a substituted orunsubstituted aryl group having 6 to 30 ring carbon atoms, and X, and R₁to R₄ are defined the same as those of Formula
 1. 19. The organicelectroluminescence device as claimed in claim 14, wherein the compoundrepresented by Formula 1 is represented by the following Formula 5:

wherein in Formula 5, W is O, S, PR₈, S═O, SO₂, P═OR₉, CR₁₀R₁₁, orSiR₁₂R₁₃, R₆ to R₁₃ are each independently a hydrogen atom, a deuteriumatom, a substituted or unsubstituted alkyl group having 1 to 10 carbonatoms, a substituted or unsubstituted aryl group having 6 to 30 ringcarbon atoms, or a substituted or unsubstituted heteroaryl group having2 to 30 ring carbon atoms, a and b are each independently an integer of0 to 4, and X, R₁ and R₄ are defined the same as those of Formula
 1. 20.The organic electroluminescence device as claimed in claim 14, whereinthe heterocyclic compound represented by Formula 1 is a compound of thefollowing Compound Group 1: